Filling The Void

Mom has been a very strong-willed woman for as long as I’ve known her. She never hesitated to play the role of the bad cop when one of us kids did something wrong. Her toughness is what propelled her to her job as president of an IT firm, a job that she took very seriously. Dad took great pride in having a wife that is one of the top people in their industry. Mom and Dad were high school sweethearts. Being in love made them decide to go to the same college and major in the same thing: IT technology. During college Mom got pregnant with me. Shortly after, Mom and Dad married. Despite having me, both Mom and Dad graduated at the top of their class. Along with being intelligent and strong-willed, Mom is extremely gorgeous. I heard from so many guys, and a few girls, in high school that Mom is the sexiest MILF ever and they’d love to have a night with her. Those comments came most often during our summer pool parties when Mom would wear her sexiest swimsuits. I must admit that I stared at her when I knew that nobody was looking my way. I will admit that I jerked off many times while thinking about Mom. Sometimes I’d grab one of her bras (34C, by the way) out of the hamper so I’d cum even harder than I would just thinking about her. I’m not sure if she ever noticed that there’d be a little cum in them sometimes when she would wash them. If she did, she never told me. Knowing how strong she is mentally is what caused me to be so shocked when she called my dorm room one morning. She was crying almost hysterically. After finally getting her somewhat calmed down I found out Dad was in the hospital after having a major heart attack. Needless to say, I dropped everything at school and flew home. I immediately dropped my classes, knowing I could return at a later date and pick up where I left off. Dad died a few days later. My sisters, twins and two years younger than me, couldn’t get back from an overseas trip until the day before the funeral. I did my best to be strong when I picked Jessie and Alexis up at the airport. Seeing them made me feel a little better. As willing as I was to do it, I hated having to be the only strong one for Mom. In the six months following the funeral, things somewhat returned to normal. Jessie and Alexis left for college, although they agreed to drive home one weekend a month. I transferred to an online university, so I could stay home with Mom. She protested at first, saying that I need the campus experience. After I refused a few times Mom said she’d love to have me home all the time. One night, shortly after settling into bed, I thought I heard something. I opened my bedroom door and walked across the hallway to Mom’s door. I heard her crying pretty hard. Without hesitation, and without knocking, I walked into the room. Mom was curled up in bed sobbing into her pillow. I rushed over, laid next to her, and held Mom close to me. Once Mom finally stopped sobbing I asked what was wrong. “I really miss your dad at night. Especially on nights like this.” “What do you mean, on nights like this,” I asked. “I’d rather not say. It’s kind of embarrassing.” “Come on, Mom. You know you can talk to me about anything. Especially now. I’m living here so we can take care of each other.” “It’s just that I’m starting to really miss the intimate part of my relationship with your dad. And it’s not just the sex. It’s the closeness I felt laying next to him.” We talked for almost an hour. I could tell Mom was exhausted, so I put my arm around her. Within minutes she was sleeping. I laid awake for a while thinking. I knew what I needed to do. I planned to take Dad’s place in Mom’s bed, emotionally and physically. All that was left was figuring out how to convince Mom to let me do it. I spent all of the next day preparing for my talk with Mom. I expected some resistance to what I would say. But, in the end, I knew logic would win out. Mom was never one to follow what society told us was right and wrong. When us kids were growing up, we were taught to not be shy about our bodies. We swam nude and showered together on numerous occasions. Mom and Dad sat us all down together to explain sex and masturbation. Mom and Dad were never quiet about sex either. At least twice a week I heard them. Mom is a real screamer too. After dinner I told Mom that we needed to talk. She told me we could after she finished with her bath. When I heard the bathwater draining I poured us each some wine and sat on Mom’s bed. As usual Mom didn’t mind me being in the room as she dressed. Mom sat on the bed next to me. “What’s up, Jacob? What’re you wanting to talk about?” “I’ve been doing a lot of thinking since last night Mom. I know that you really miss the intimate part of being with Dad. I have an idea, but you need to promise me that you won’t freak when I tell you.” “Of course, I promise.” “What would you say to me taking Dad’s place as your partner in bed?” “What?! Why would you ask that? You’re my son!” “I know. That’s why I suggested it. There’s no better person for that job right now. I love you and I wanna make you happy, in that way if need be.” “But it’s wrong, Jacob!” “Says who? Society? You’ve always taught me and the twins that society’s rules aren’t always right. I think this is right. Besides, it’s not like the world would find out. Unless you brag about your sex life. Do you?” “Of course not.” “Well, then why can’t we share your bed in every way?” “It’s just that this is a lot to take in right now. I’m not saying no. I am saying let me think about this tonight and we’ll discuss it more in the morning.” I barely slept that night. I tossed and turned a lot. My conversation with Mom played over and over in my head. It didn’t sound promising at the moment, but I was gonna let Mom think it over. I hoped she would see that this is the right thing for us. During breakfast the next morning Mom made an offer. “Jacob, I thought about your offer all night long. I agree that it shouldn’t matter what society says about what we do. I also agree that you’d be the best person to take your dad’s place in my bed. There’s no man I trust more than you right now. I’m just not sure about sex. Before I say anymore, could I ask one question?” “Of course, Mom.” “Are there any other reasons why you want to share my bed with me?” “There is a part of me that really wants to have sex with you. I’ve wanted to since high school. Since I started liking girls I’ve thought you were the most beautiful woman I’ve ever seen. I still think that. There were many times I thought about you as I masturbated. I hope hearing this isn’t too much to take in.” “I’m glad you admitted it. I know you used to do that. I also know you borrowed my bras sometimes when you masturbated. I was uncomfortable with that at first, but your dad told me that was normal for a teenage boy.” We talked some more and agreed that I’d sleep in her bed for as long as she wanted me to. A part of me was disappointed that there would be no sex. But I was doing this for Mom, so I could live with that. I figured this would ring us closer together too. That night we both got ready for bed in her bedroom, me beside the bed and Mom in her walk-in closet. When Mom finished and walked out, the sight of her took my breath away. She was in an almost sheer blue nightie with a matching thong underneath. I had never seen a more gorgeous woman in my entire life. “Like what you see?” “My God, you look so amazing! But why dress in such a revealing nightie where I can see you?” “I’ve missed the reaction I used to get from you dad. I thought about how you used to masturbate to my bras and figured I might get that reaction from you. Do you really like how I look?” “Mom, you always look gorgeous to me but right now you look so breathtakingly beautiful. Come on. Let’s both get some sleep.” We laid down and within minutes Mom was asleep and lightly snoring. I couldn’t help but just stare at her, watching every inch of her body. I loved seeing her breasts move with each breath she took. I could definitely see what made Dad fall in love with her. Some time after falling asleep I felt something that startled me awake. It took a minute to remember that I was in Mom’s bed. I realized that it was her arm around my shoulder. Mom must’ve instinctively put it there, forgetting it was me laying beside her, not Dad. As I was about to gently move her arm Mom drew in closer, eliminating the gap between us. I knew that pushing Mom away might wake her up and freak her out. Mom then began running her hand lightly across my chest. I was very conflicted at that moment. On one hand, I really wanted to see where this went. But on the other hand, I didn’t want Mom going farther than she wanted with me. That could screw up our great relationship. I just laid there letting her stay where she was. There was one problem that I wasn’t quite sure how to resolve. I was beginning to get hard. Feeling her breasts against my bad felt so good and I knew it wouldn’t be long before I was rock hard. My cock was rock hard and hurting in a few minutes, like I figured. I took a chance and reached down so I could relieve myself. I slowly began to stroke my six-and-a-half-inch cock. I imagined myself rolling over to face Mom, removing her nightie, then stroking a breast. As I massage her breasts, one at a time, her nipples become little pebbles between my fingers. I then imagine myself reaching down and inserting my free hand into her panties. Light moans escape her mouth as I flick and pinch her clit. My fantasy ended abruptly when Mom spoke. “If you really want to we can do something together.” “But I thought you didn’t want that Mom.” “I wanted to make sure first that you weren’t trying to take advantage of my sadness first. After I wrapped my arm around you and pushed in close you didn’t try anything.” “How far are you willing to go, Mom?” “Could we just start by kissing and rubbing each other? I really loved doing that with your dad and I miss it so much.” Without replying I helped her remove her nightie and her panties. Then Mom helped me remove my shorts. We then shared a very long, very passionate kiss. It was better than I could have imagined. Mom’s lips and tongue mingled with mine, our hands groping each other in the process. I focused on Mom’s nipples. They were bigger than I figured, and I loved it. As they hardened I pinched them harder. Mom reached down and grasped my painfully hard cock. She began stroking, lightly at first. As her hand reached the head, she squeezed it. The sight of my own mother stroking me had me close to cumming fast. I had to concentrate on what I was doing to Mom so I wouldn’t burst early. It was time for me to work on Mom’s pussy. As I got a good look at it, I saw the most beautiful pussy I had ever seen. The first thing I noticed was a small patch of trimmed hair that was as red as the hair on her head. As my eyes went farther down I saw her clit. It was a tad bigger than any of the girlfriends I’ve had. I knew immediately that I would really enjoy playing with it. Mom’s pussy looked a little tighter than I expected for a woman her age. I used my fingers to massage Mom’s pussy as my thumb rubbed her clit. The look in Mom’s eyes and the moans emanating from her mouth told me I was doing it right. I kept at a slow pace for about five minutes. By that time Mom was stroking me faster, squeezing every other stroke. It was feeling so intense and I knew I would cum very soon. In order to speed up Mom’s orgasm I knew I’d need to work fast. I inserted two fingers and started fingering her very fast, putting pressure on her clit at the same time. Within seconds Mom’s free hand was grasping her sheet and her stroking of my cock stopped. A few seconds later a hurricane of an orgasm rushed through her with a force I had never seen in a woman. Mom’s eyes rolled back and she was bucking so wildly that I could barely keep my hands on her pussy. I managed to keep fingering though. “Stop! Feels too good!” I stopped and let her come down from her orgasm, stroking a little as I watched her. After she rested she continued stroking me. Mom did something I would never have expected. She reached down and rubbed her pussy so her juices would be on her fingers. She then rubbed them onto my cock, getting her juices on it. I knew I’d cum soon. Mom started stroking very fast, massaging my balls with her other hand. That was all I needed. My cock erupted with enough force that I was unable to focus on anything other than the intense pleasure. The orgasm shot all through me, feeling so incredible. I laid next to Mom after my orgasm ended. We held each other and talked until we fell asleep.